CN106633860B - Low-k liquid-crystal polyester resin compound and preparation method thereof - Google Patents
Low-k liquid-crystal polyester resin compound and preparation method thereof Download PDFInfo
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- CN106633860B CN106633860B CN201611244220.4A CN201611244220A CN106633860B CN 106633860 B CN106633860 B CN 106633860B CN 201611244220 A CN201611244220 A CN 201611244220A CN 106633860 B CN106633860 B CN 106633860B
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/12—Polyester-amides
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2207/00—Properties characterising the ingredient of the composition
- C08L2207/06—Properties of polyethylene
- C08L2207/068—Ultra high molecular weight polyethylene
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Abstract
The present invention provides a kind of low-k liquid-crystal polyester resin compounds, are made of the following component of following parts by weight, and 60-90 parts of liquid-crystal polyester resin；1-10 parts of additive；10-40 parts of filler, wherein, the liquid-crystal polyester resin is all aromatic liquid crystal polyester resin, the all aromatic liquid crystal polyester resin is polymerized by reaction monomers, and the reaction monomers include at least one of free aromatic diamine and aromatic series azanol, aromatic hydroxy-carboxylic or aromatic amine yl carboxylic acid, aromatic diol and aromatic dicarboxylic acid；The additive is ultra-high molecular weight polyethylene, and the number-average molecular weight of the ultra-high molecular weight polyethylene is 1,150,000-590 ten thousand.
Description
Technical field
The invention belongs to field of polymer composite material more particularly to a kind of low-k liquid-crystal polyester resin compounds
And preparation method thereof.
Background technique
In recent years, with the high speed development of electronics and information industry, the development trend of electronic equipment high frequency is more obvious, especially
It is electronic product, the high speed development for communicating product, satellite transmission, information products move towards high speed and high frequency, superior high frequency
Electronic component needs the material of higher performance to lay a foundation, therefore to all aromatic liquid crystal polyester resin as electronic component raw material
(LCP) more stringent requirements are proposed for performance.The high frequency tolerant characteristic of material is that dielectric properties determine, dielectric constant (Dk) is necessary
Small and very stable, the transfer rate of signal and the square root of material dielectric constant are inversely proportional, and high dielectric constant be easy to cause letter
Number transmission delay.And the dielectric properties of previous LCP compound are excellent not enough, it is therefore desirable to there is lower dielectric constant, with
Reduce power consumption penalty and better Electronic Performance to the greatest extent.
Summary of the invention
The purpose of the present invention is to provide a kind of low-k liquid-crystal polyester resin compounds and preparation method thereof, it is intended to
Solve the problems, such as that liquid-crystal polyester resin compound dielectric properties are bad.
The invention is realized in this way a kind of low-k liquid-crystal polyester resin compound, by following parts by weight
Following component composition,
60-90 parts of liquid-crystal polyester resin；
1-10 parts of additive；
10-40 parts of filler,
Wherein, the liquid-crystal polyester resin is all aromatic liquid crystal polyester resin, all aromatic liquid crystal polyester resin
It is polymerized by reaction monomers, the reaction monomers include at least one of free aromatic diamine and aromatic series azanol, virtue
Fragrant race's hydroxycarboxylic acid or aromatic amine yl carboxylic acid, aromatic diol and aromatic dicarboxylic acid；The additive is super high molecular weight
Polyethylene, and the ultra-high molecular weight polyethylene number-average molecular weight is 1,150,000-590 ten thousand.
And a kind of preparation method of low-k liquid-crystal polyester resin compound, comprising the following steps:
Each component is weighed according to the formula of above-mentioned low-k liquid-crystal polyester resin compound, wherein the additive
For ultra-high molecular weight polyethylene, and the ultra-high molecular weight polyethylene number-average molecular weight is 1,150,000-590 ten thousand；
The all aromatic liquid crystal polyester resin, additive, filler are dried；
The additive, filler after drying is uniformly mixed, mixture is obtained；
The mixture and all aromatic liquid crystal polyester resin are subjected to feeding processing, melted through double screw extruder
Extrusion, tie rod, cooling, granulation processing.
Low-k liquid-crystal polyester resin compound provided by the invention, with heat resistance, excellent mechanical performance
And electrical insulating property.Therefore all aromatic liquid crystal polyester resin dielectric constant provided by the invention is low, while having excellent bending
Performance.It can be used as the raw material of high frequency electronic component.
The preparation method of low-k liquid-crystal polyester resin compound provided by the invention, only need to will be first by liquid crystal polyester
It after resin, additive, filler are dried, then by additive, filler mixing, is mixed with liquid-crystal polyester resin, carries out melting and squeeze
Out, being granulated can be obtained, the technical maturity, and method is simply controllable, it is easy to accomplish industrialization.Importantly, the present invention with
Ultra-high molecular weight polyethylene has good compatibility as additive, with liquid-crystal polyester resin, made without adding compatilizer
The low-k liquid-crystal polyester resin compound dielectric constant obtained reduces, while having excellent bending property, can be used as height
Band electronic component raw material.
Specific embodiment
In order to which technical problems, technical solutions and advantageous effects to be solved by the present invention are more clearly understood, below in conjunction with
Embodiment, the present invention will be described in further detail.It should be appreciated that specific embodiment described herein is only used to explain
The present invention is not intended to limit the present invention.
The embodiment of the invention provides a kind of low-k liquid-crystal polyester resin compounds, by under following parts by weight
Column group is grouped as,
60-90 parts of liquid-crystal polyester resin；
1-10 parts of additive；
10-40 parts of filler,
Wherein, the liquid-crystal polyester resin is all aromatic liquid crystal polyester resin, all aromatic liquid crystal polyester resin
It is polymerized by reaction monomers, the reaction monomers include at least one of free aromatic diamine and aromatic series azanol, virtue
Fragrant race's hydroxycarboxylic acid or aromatic amine yl carboxylic acid, aromatic diol and aromatic dicarboxylic acid；The additive is super high molecular weight
Polyethylene, and the ultra-high molecular weight polyethylene number-average molecular weight is 1,150,000-590 ten thousand.
Specifically, it is excellent to assign the compound as matrix composition for the liquid-crystal polyester resin in the embodiment of the present invention
Heat resistance, dimensional stability and high-mechanical property.In the embodiment of the present invention, the liquid-crystal polyester resin is Wholly aromatic liquid crystal
Polyester resin, all aromatic liquid crystal polyester resin of the range of number-average molecular weight at 30000-60000, height polymerization have high fever
Stability, excellent mechanical performance and electrical insulating property.
All aromatic liquid crystal polyester resin described in the embodiment of the present invention is polymerized by reaction monomers, specifically, described anti-
Answering monomer includes at least one of free aromatic diamine and aromatic series azanol, aromatic hydroxy-carboxylic or aromatic series aminocarboxylic
Acid, aromatic diol and aromatic dicarboxylic acid.There is all aromatic liquid crystal polyester resin of above-mentioned monomer composition, higher opposite
There is better thermal stability and intensity under creepage trace index.
Specific preferred, the liquid-crystal polyester resin contains at least one of following repetitive units:
Repetitive unit from aromatic diol :-O-Ar-O-；
Repetitive unit from aromatic diamine :-HN-Ar-NH-；
Repetitive unit from aromatic series azanol :-HN-Ar-O-；
Repetitive unit from aromatic dicarboxylic acid :-OC-Ar-CO-；
Repetitive unit from aromatic hydroxy-carboxylic :-O-Ar-CO-；
Repetitive unit from aromatic amine yl carboxylic acid :-HN-Ar-CO-；
Wherein, the Ar be penylene and its derivative, biphenylene and its derivative, naphthalene and its derivative, two penylenes by
One of aromatic compound and its derivative that carbon or the element of non-carbon are bonded, the derivative of meaning of the embodiment of the present invention
Object refers to the aromatic compound that the penylene, biphenylene, one or more hydrogen atoms on naphthalene are replaced by other elements.
As specific embodiment, the content of the liquid-crystal polyester resin is 60-90 parts, concretely 60 parts, 65 parts, 70
Part, 75 parts, 80 parts, 85 parts, the specific deals such as 90 parts.
In the embodiment of the present invention, the additive is ultra-high molecular weight polyethylene, and its number-average molecular weight is 1,150,000-590
Ten thousand, to assign the liquid-crystal polyester resin compound excellent electrical insulating property and workability.It is described as specific embodiment
The content of additive is the specific deals such as 1-10 parts, concretely 1 part, 2 parts, 3 parts, 5 parts, 8 parts, 10 parts.
The mechanical performance of compound, hot property can be enhanced in the filler.The preferred filler is glass fibre, crystalline substance
At least one of palpus, carbon fiber.As specific embodiment, the content of the filler is 10-40 parts, concretely 10 parts, 15
Part, 20 parts, 25 parts, 30 parts, 35 parts, the specific deals such as 40 parts.
It should be noted that the content of each addO-on therapy need to meet above-mentioned requirements, if content mistake in the embodiment of the present invention
It is low, it is difficult to it is corresponding to play the role of it；If content is too high, will increase into instead in the case where the effect that it is played reaches saturation
Originally, it even will affect other performances, influence the quality of the liquid-crystal polyester resin compound instead.
Low-k liquid-crystal polyester resin compound provided in an embodiment of the present invention has heat resistance, excellent machinery
Performance and electrical insulating property.All aromatic liquid crystal polyester resin dielectric constant provided by the invention is low, while having excellent bending
Performance.It can be used as the raw material of high frequency electronic component.
Low-k liquid-crystal polyester resin compound provided in an embodiment of the present invention can be prepared by following methods and be obtained
?.
And the embodiment of the invention provides a kind of preparation method of low-k liquid-crystal polyester resin compound, packets
Include following steps:
S01. each component is weighed according to the formula of above-mentioned low-k liquid-crystal polyester resin compound, wherein described to add
Adding agent is ultra-high molecular weight polyethylene, and the number-average molecular weight of the ultra-high molecular weight polyethylene is 1,150,000-590 ten thousand；
S02. all aromatic liquid crystal polyester resin, additive, filler are dried；
S03. the additive, the filler after drying are uniformly mixed, obtain mixture；
S04. the mixture and all aromatic liquid crystal polyester resin are subjected to feeding processing, through double screw extruder
Melting extrusion, tie rod, cooling, granulation processing.
Specifically, in above-mentioned steps S01, the formula of the low-k liquid-crystal polyester resin compound and its it is each preferably
Situation, as described above, in order to save length, details are not described herein again.
As specific embodiment, all aromatic liquid crystal polyester resin is prepared by following methods, is specifically included
Following steps:
S011., at least two reaction monomers are provided, polycondensation reaction is carried out and prepares liquid crystal polyester prepolyer；
S012. liquid-crystal polyester resin is prepared in liquid crystal polyester prepolymer progress solid phase polycondensation.
In above-mentioned steps S011, the reaction monomers are as described above.As preferred implementation, the polycondensation reaction is being carried out
Before, it further include that the reaction monomers are pre-processed using acylation agent.The reaction monomers can be improved by pretreatment
Reactivity, specifically, the acylation agent includes but is not limited to acetyl group agent, the acetyl group agent can will be described anti-
It answers monomer to carry out acetylation process, improves its reactivity.
The polycondensation reaction can be adopted and be realized with the conventional methods in the field, including but not limited to solution polycondensation, ontology
Condensation methods.
In above-mentioned steps S012, the solid state condensation reaction needs to be heated to above-mentioned liquid-crystal polyester resin prepolymer
Processing.But specific heating temperature, it is variant because of the selected reaction monomers, it can not limit together herein.It is described
Heat treatment can pass through the methods of heating plate, hot wind, high temperature fluid.In addition, in order to remove the by-product of solid state condensation reaction, it can
Using inert gas purge or utilize vacuum removing.
In above-mentioned steps S02, in order to avoid water content mistake in all aromatic liquid crystal polyester resin, additive, filler
Height adversely affects the low-k liquid-crystal polyester resin composite properties of preparation, needs the liquid crystal polyester tree
Rouge, additive, filler are dried.Preferably, the temperature of the drying process is 120-140 DEG C, drying time 3-5
Hour, more preferably 4 hours.
In above-mentioned steps S03, the additive, filler are uniformly mixed, and automatic blender realization can be used in mixing, certainly,
Other, which can also be used, can realize that mixed uniformly mode is realized.
In above-mentioned steps S04, the mixture and all aromatic liquid crystal polyester resin are subjected to feeding processing, preferably
It is fed from different spouts, to improve mixing uniformity.At double screw extruder melting extrusion, tie rod, cooling, granulation
Reason, can be obtained all aromatic liquid crystal polyester resin compound.
The preparation method of low-k liquid-crystal polyester resin compound provided in an embodiment of the present invention, only need to will be first by liquid
After brilliant polyester resin, additive, filler are dried, then by additive, filler mixing, mix, carry out with liquid-crystal polyester resin
Melting extrusion, granulation can be obtained, the technical maturity, and method is simply controllable, it is easy to accomplish industrialization.Importantly, this
Inventive embodiments have good compatibility using ultra-high molecular weight polyethylene as additive, with liquid-crystal polyester resin, without adding
Add compatilizer, obtained low-k liquid-crystal polyester resin compound dielectric constant reduces, while having excellent bending
Performance can be used as high frequency electronic component raw material.
It is illustrated combined with specific embodiments below, wherein all aromatic liquid crystal polyester resin is new by Jiangsu water
Material manufactures limited public company and provides, and polyethylene is that (molecular weight linear gathers Million 145M in 1,150,000 or more unbranched
Ethylene).
Embodiment 1
A kind of low-k liquid-crystal polyester resin compound, each group containing weight percentage shown in 1 embodiment 1 of table
Point.
The preparation method of the low-k liquid-crystal polyester resin compound, comprising the following steps:
S11. each component is weighed according to the formula of above-mentioned all aromatic liquid crystal polyester resin compound；
S12. all aromatic liquid crystal polyester resin, additive, filler are dried 4 hours at 130 DEG C；
S13. the additive, the filler after drying are put into automatic blender and is uniformly mixed, obtain mixture；
S14. the mixture and all aromatic liquid crystal polyester resin are subjected to feeding processing, through double screw extruder
Melting extrusion, tie rod, cooling, granulation processing.
Embodiment 2
A kind of low-k liquid-crystal polyester resin compound, each group containing weight percentage shown in 1 embodiment 2 of table
Point.
The preparation method of the low-k liquid-crystal polyester resin compound, it is same as Example 1.
Embodiment 3
A kind of low-k liquid-crystal polyester resin compound, each group containing weight percentage shown in 1 embodiment 3 of table
Point.
The preparation method of the low-k liquid-crystal polyester resin compound, it is same as Example 1.
Comparative example 1
A kind of low-k liquid-crystal polyester resin compound, each group containing weight percentage shown in 1 comparative example 1 of table
Point.
The preparation method of the low-k liquid-crystal polyester resin compound, it is same as Example 1.
Low-k liquid-crystal polyester resin compound prepared by 1-3 of the embodiment of the present invention and comparative example 1 is as injection molding
Then raw material is tested for the property using injection moulding machine injection molding, the method for performance test is as follows:
(1) it dielectric constant: is tested by ASTM D-150, test frequency 1KHz, 1MHz and 1GHz.
(2) it bending strength: is tested by ASTM D-790.
Test result is as follows shown in table 2.
Table 1
Table 2
By upper table 2 as it can be seen that the low-k liquid-crystal polyester resin compound manufactured in embodiment 1-3 is relative to comparative example
The liquid-crystal polyester resin compound manufactured in 1 influences less dielectric constant in 1KHz, but in 1MHz and 1GHz, this hair
The dielectric constant of bright low-k liquid-crystal polyester resin compound reduces, and has excellent bending property.Therefore, of the invention
The raw material that the low-k liquid-crystal polyester resin compound of offer can be used as high frequency electronic component uses, but not only limit application
In this.
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Made any modifications, equivalent replacements, and improvements etc., should all be included in the protection scope of the present invention within mind and principle.
Claims (8)
1. a kind of low-k liquid-crystal polyester resin compound, which is characterized in that by the following component group of following parts by weight
At,
60-90 parts of liquid-crystal polyester resin；
1-10 parts of additive；
10-40 parts of filler,
Wherein, the liquid-crystal polyester resin is all aromatic liquid crystal polyester resin, and all aromatic liquid crystal polyester resin is by anti-
Monomer polymerization is answered to form, the reaction monomers include at least one of free aromatic diamine and aromatic series azanol, aromatic series
Hydroxycarboxylic acid or aromatic amine yl carboxylic acid, aromatic diol and aromatic dicarboxylic acid；The additive is superhigh molecular weight polyethylene
Alkene, and the number-average molecular weight of ultra-high molecular weight polyethylene is 1,150,000-590 ten thousand.
2. low-k liquid-crystal polyester resin compound as described in claim 1, which is characterized in that the liquid crystal polyester tree
Rouge contains at least one of following repetitive units:
Repetitive unit from aromatic diol :-O-Ar-O-；
Repetitive unit from aromatic diamine :-HN-Ar-NH-；
Repetitive unit from aromatic series azanol :-HN-Ar-O-；
Repetitive unit from aromatic dicarboxylic acid :-OC-Ar-CO-；
Repetitive unit from aromatic hydroxy-carboxylic :-O-Ar-CO-；
Repetitive unit from aromatic amine yl carboxylic acid :-HN-Ar-CO-；
Wherein, the Ar be penylene and its derivative, biphenylene and its derivative, naphthalene and its derivative, two penylenes by carbon or
One of aromatic compound and its derivative that the element of non-carbon is bonded.
3. low-k liquid-crystal polyester resin compound as described in claim 1, which is characterized in that the filler is glass
At least one of fiber, whisker, carbon fiber.
4. a kind of preparation method of low-k liquid-crystal polyester resin compound, comprising the following steps:
Each component is weighed according to the formula of the low-k liquid-crystal polyester resin compound as described in claim 1-3 is any,
In, the additive is ultra-high molecular weight polyethylene, and the ultra-high molecular weight polyethylene number-average molecular weight is 1,150,000-590
Ten thousand；
The all aromatic liquid crystal polyester resin, additive, filler are dried；
The additive, filler after drying is uniformly mixed, mixture is obtained；
The mixture and all aromatic liquid crystal polyester resin are subjected to feeding processing, melts and squeezes through double screw extruder
Out, tie rod, cooling, granulation processing.
5. the preparation method of low-k liquid-crystal polyester resin compound as claimed in claim 4, which is characterized in that described
The temperature of drying process is 130-160 DEG C.
6. the preparation method of low-k liquid-crystal polyester resin compound as claimed in claim 4, which is characterized in that described
All aromatic liquid crystal polyester resin is prepared by following methods, specifically includes the following steps:
At least two reaction monomers are provided, polycondensation reaction is carried out and prepares liquid crystal polyester prepolyer；
Liquid-crystal polyester resin is prepared in liquid crystal polyester prepolymer progress solid phase polycondensation.
7. the preparation method of low-k liquid-crystal polyester resin compound as claimed in claim 6, which is characterized in that described
The method of polycondensation reaction is solution polycondensation or bulk polycondensation method.
8. the preparation method of low-k liquid-crystal polyester resin compound as claimed in claims 6 or 7, which is characterized in that
The reaction monomers are pre-processed using acylting agent.
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| US12035467B2 (en) | 2023-06-27 | 2024-07-09 | Ticona Llc | Circuit structure |
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| US11637365B2 (en) | 2019-08-21 | 2023-04-25 | Ticona Llc | Polymer composition for use in an antenna system |
| US11258184B2 (en) | 2019-08-21 | 2022-02-22 | Ticona Llc | Antenna system including a polymer composition having a low dissipation factor |
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| KR20220145385A (en) | 2020-02-26 | 2022-10-28 | 티코나 엘엘씨 | circuit structure |
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| US5643988A (en) * | 1993-12-28 | 1997-07-01 | Toray Industries, Inc. | Shaped article of liquid crystalline polymer |
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